: This research proposal outlines studies aimed toward the design and development of an efficient catalytic and enantioselective method towards the synthesis of various members of the pyrrolizidine class of alkaloids. Interest in this class of compounds stems from their potential clinical applications as antiviral and antiretroviral agents. The proposed synthesis highlights a novel approach to the enantioselective construction of the 1-azabicyc1o (3.3.0) octane nucleus of the pyrrolizidine alkaloids; this will be achieved through asymmetric ring-opening/ring-closing metathesis of achiral 7-azabicyclo(2.2.1)hepta-2,5-dienes.